1. “I didn't know really how you were supposed to go about things, so I think I mostly made the bed move instead of using my hips. Like, the bed did all the fucking for me.” — Tyler, 26

2. “Why are you asking this? A better question would be, ‘does anyone actually have any cool stories about losing their virginity?” — Chris, 28

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3. “I know this isn’t that awkward and it happens, but I finished in maybe five seconds. It was only awkward because I [let my partner assume] that I wasn’t a virgin. I overestimated my first-time stamina.” — Luke, 26

4. “I lost my virginity to my best friend’s girlfriend. Everyone is an ex now. 'Ex-best friend and his ex-girlfriend' is really how I should introduce this. I was desperate. I really wanted to lose my virginity, and somehow, for some reason, my friend’s girlfriend had a thing for me. I think she felt bad for me. The sex was fine, but I felt so bad afterwards, and for good reason. It was years ago, but I still don’t really have a fond memory of losing it.” — Mark, 29

5. “I couldn’t get the condom on. I was probably goofing around that day in health class or something, because I was just drawing a blank. I think the first time I unrolled it completely and then tried to slide it on. I definitely tore one or two. It wasn’t too bad, but I remember being worried I was going to blow my chance by ruining all the condoms and then we wouldn’t be able to have sex.” — Phil, 28

6. “My mom walked in. It was on a family vacation and I got to bring my girlfriend and we thought we had the hotel room to ourselves for the afternoon. Nope. Like, my mom is pretty cool, but that put a damper on the rest of the trip. There are some milestones you want your mom to be there for, like graduation. Losing your v-card isn’t one of those milestones.” — Steve, 29

7. “I uh…. entered the wrong hole. For some reason, she was really nice about it and didn’t say anything right away? It was a lubed up condom but it was making her really uncomfortable. I really didn’t go in far, but I was thinking, ‘Oh wow, I must have such a big dick...’ I was so proud of myself. She had to stop me and tell me what was going on. I remember thinking at the time that it was such a rookie maneuver, but now I’m older and wiser and know it wasn’t such a big deal.” — Nathan, 27

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8. “I literally, not figuratively, but literally came as soon as I entered her. We very stupidly decided to do it despite not having condoms and spent more time Googling about getting pregnant than we did actually having sex.” — Brett, 29

9. “I didn’t know what to do with the condom afterwards so I threw it in my garbage can in my room. Honestly, in hindsight I wish I threw it in the woods or something. That would’ve been better. But my parents found it and grounded me. The idea that my mom found my used condom still makes my skin crawl.” — Jon, 27

10. “I guess as far as how bad this could have gone it’s not the worst but it still takes me to a dark place. For context, you need to understand that I was in high school. It was summer and I was doing tons of dumb shit, because I had just gotten my driver’s license. There was a local chicken wing place that had one of those super hot sauces that they really hyped up; there was a challenge to eat 20 of them, and you had to sign a waiver, all of that. Anyway, my friends and I decided to order a bucket for lunch and try and get through them. It was dumb teenager stuff, it was a lot of fun, and we managed to finish the whole thing. Later that night, I get a call from the girl I had a crush on, parents aren’t home and all that. But we’re making out, we both decide this is going to happen. I’m all excited. We’re doing it. We’re taking it slow. And my stomach starts rumbling. We’re in missionary, and I’m doing my best to hold it, and I’m staring into this girl’s eyes and trying to be movie-sex-scene romantic. And I fart. And I don’t want to get gross, but it’s this loud, long, wet cartoon fart. And I’m staring at her. And she’s staring at me. And I don’t know how long it really was, but I swear to you, looking back it felt like forever. It was reasonably 10 seconds of just me and my cartoon sound effect fart. She laughed and was cool about it at the time, but we never quite rekindled that romance.” — Marc, 28

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